Let’s just state the obvious: The prom dress in Pretty in Pink, the Molly Ringwald/John Hughes film that opened on this day in 1986, is a dog. In fact, given that the title of the film is based around the climatic scene where Ringwald’s character, Andie, arrives at the prom in a pink dress of her own design, the garment’s puckered seams and unflattering cut becomes the second biggest surprise of the film (I won’t reveal the other surprise, in case you haven’t already seen the grotesque ending). And yet, ultimately, the dress’s inadequacies are fitting. In this film about a studious high-school girl from the wrong side of the tracks (Hughes has actual railroad tracks running by her house, in case you didn’t pick up on the poverty angle early on) who falls for a rich boy, Andie’s shortcomings are as numerous as her assets, and the wardrobe successfully mirrors that dichotomy throughout.

Ringwald was already an indie teen favorite by the time Pretty in Pink came out, having charmed with her California punk-pop wardrobe in Sixteen Candles and breezy style in The Breakfast Club. Thanks to costume designer Marilyn Vance, Hughes 80s-era films consistently showcase teenage characters in authentic and cheeky outfits, underscoring the writer’s famously earnest dialogue. Vance excels at capturing, without irony or kitsch, the instinctive thrift and experimental, sometimes awkward dressing that is distinctive to adolescents.In Pretty in Pink, for example, Andie overcomes a lack of monetary resources with creative ones: She shops second-hand and sews her own clothes (is this the first teenager depicted in a film to do so? I can’t think of another). Her character is self-sufficient and driven, earning straight-As while dutifully taking care of her unshaven, stymied father and working at a record store after school. (Andie is also passive aggressive—“Daddy, what are you doing up this early? I didn’t wake you up!”—and a total kiss-ass—“I’m lucky the good people of this community allow me to have this education!”—but Hollywood doesn’t offer much in the way of teenage-girl role models, so we take what we can get.)
And Vance deftly captures Andie’s complex personality in wardrobe. Her character’s granny-chic style is an ongoing balance of Andie appearing steady and brainy as well as artsy and alienated. Andie longs to live in a big house and find a place in mainstream society, but is also repulsed by the rich students and their slutty, Miami Vice–inspired style. So she over-compensates by over-accessorizing, and creates an insurmountable wall of asexualization and disinterest in the process: A large hat is roughly knotted with a fabric remnant; an already studious blouse is fastened with a cheap brooch and topped with a worn crochet vest; a cardigan atop another cardigan is trimmed with broken charms from an old bracelet. Andie favors dowdy textiles: florals, lace, knits and, you guessed it, a virginal shade of pink. At school, the piled-on effect is entirely repellent, while during her off-hours at work, at home or hanging out with friends, the look relaxes into a style that is funky and flattering.
Although we learn early on that Andie makes her own clothes, she never actually claims to want to become a fashion designer, but the idea is implied. So when the scene arrives where Andie sits down with a big drawing pad to sketch out her prom dress, it’s a surprise to see that her talents are nowhere near as developed as we might have believed. Her illustration, a sort of See-Jane-Wear-Prom-Dress-meets-Klaus-Nomi, is five arrow-straight lines forming a polygon topped with a Jetsons-style collar. Even more remarkable, after Andie free-saws through the fabric without the aid of a pattern, the finished dress looks almost exactly like the rudimentary drawing! The boxy gunny sack with its single, forward-thinking feature is pink, of course, a merging of a tacky, cheap dress her father bought and a beautiful, vintage dress her friend gave her.
But the result feels like a let down. The audience is expecting Andie to emerge as a goddess and gets…Andie, just in a shinier, even more pink, version. Yet, there is something undeniably sweet about the homemade dress. It is awkward, complicated and unattractive, which is, frankly, like Andie herself. But she has also stripped off her usual blanket of layers and exposed herself to her enemies. She wears no crazy hat or shawl or excessive jewelry. The character cannot draw or sew very well, we learn far too late, and has few resources, so what you see is what you get. It would have been a bogus Hollywood move to put Andie in a sexy show-stopper, and yet you still can’t help but root for something a bit more dazzling. Perhaps my view on the dress is hypocritical and contradictory, but so is the film, over and over again.
An entire post could be written about the excellent wardrobes of the other lead characters. Iona (Annie Potts) is the film’s true sartorial star, wearing leather one day and 40s era vintage the next with the aplomb of a true stylista. The brash patterns and bold colors of Duckie’s (Jon Cryer) outfits express his character’s confidence: Unlike Andie, he knows who he is and what he wants. Blane (Andrew McCarthy), Andie’s mealy love interest, and his slimy best friend, Steff (James Spader), look casually despicable in rumpled suits that hearken the seedy side of American Gigolo.
As a film, Pretty in Pink has its problems. The script is weak and cringe worthy, while the characters we are supposed to sympathize with are so maddeningly shallow or obnoxious that even the actors—save excellent performances from Cryer, Potts and Spader—can’t save them. But the costumes consistently soar. It’s a shame Vance wasn’t nominated for any awards for this film—in fact she’s only been nominated for one Oscar, for The Untouchables in 1987, and has received just three other nominations and one win, despite creating costumes for many of the most stylish movies of the 1980s and 90s. —Ali Basye

Cinemode is OTDIF’s ongoing compilation of the world’s most stylish films, a must-see list for fans of fashion. From Klute to Breakfast at Tiffany’s to Shaft, some of the greatest style inspiration comes from the characters and costumes in film. Bookmark Cinemode and check back often to read the growing list. The reviews, written with an eye specifically toward fashion, are added to On This Day In Fashion on the anniversary of the film’s release date.

I have to admit that I hated the dress more before I sat down to write about it. The more I thought about her resources at hand the more authentic the dress seemed, and the kinder I felt toward it. And I appreciate a teenager who doesn’t feel the need to look sexy every second of the day. But still. I just can’t help but want something more flattering for Andie! It’s her big moment and she looks too dumpy.

Yeesh, yeah definitely not the most flattering prom dress ever. I wish she had just worked the vintage dress into a more manageable, 80’s look. I still love this movie though, and the dress does make sense from a high school point of view. I also love the New Order song that plays while she is chopping away! There is a great episode of Veronica Mars where a character wears the exact dress to an 80’s prom, check it out!

I love Veronica Mars! And I love the music in Pretty in Pink. And, yes, I try not to judge the fashion of high-school kids too harshly. They are still developing their style and should be allowed to experiment and fail—even when they are high schoolers in movies, not real ones!

Ali, I am so glad you went into so much depth on this film — and yes, I’ll have to rent it and see it again, as it’s been over a decade. Her dress, a disappointment, if one thought she would become a fashion designer, yet you were right to juxtapose the inadequacies of “the dress” with Andie’s personal dichotomy. Trying, learning, making mistakes, … all part of being in high school. Thanks for all the wonderful pictures — it was all brought back. And this review, was enjoyable in its depth. Thanks.

“She shops second-hand and sews her own clothes (is this the first teenager depicted in a film to do so? I can’t think of another)”

Probably not the happiest example, but Sissy Spacek sews all her own clothes in “Carrie”. Actually, her prom dress wasn’t bad at all. Maybe Andie’s dress should have been the one to get that bucket over it…

i think you are so wrong. You clearly don’t understand the film at all, or the emotions in it. I think it’s beautiful and inspiring, ll the different styles so tightly packed into one film. It’s ecclectic and crzy, fair enough, but if you don’t get andie’s style taht just makes you as ignorant and judging as the rest of the kids at her school

I looked at her and I saw me. That is rare for a movie, any movie. I understand. It makes me a bit emotional, to be honest, seeing that eclectic style without the sexy, with just the individuality that makes it our own absurd style and not someone else.